1,4-Dioxane hydrochloride → HCID 67503660, compound

HRID 1047048Notes

Reaction equation

HRID 1047048 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([C:12]2[N:13]=[C:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[NH:18][C:17]4[N:25]=[CH:26][CH:27]=[CH:28][C:16]=4[N:15]3[C:29]=2[C:30]2[CH:35]=[CH:34][C:33]([C:36]3([NH:40]C(=O)OC(C)(C)C)[CH2:39][CH2:38][CH2:37]3)=[CH:32][CH:31]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3].[ClH:48].O1CCOCC1>C(Cl)Cl>[ClH:48].[ClH:48].[ClH:48].[NH2:40][C:36]1([C:33]2[CH:32]=[CH:31][C:30]([C:29]3[N:15]4[C:16]5[CH:28]=[CH:27][CH:26]=[N:25][C:17]=5[NH:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=5[C:14]4=[N:13][C:12]=3[C:8]3[CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:11]=[CH:10][CH:9]=3)=[CH:35][CH:34]=2)[CH2:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087671HCID 69087671, compound

Product 1

HCID 67503660HCID 67503660, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {1-[4-(2-{3-[(methylsulfonyl)amino]phenyl}-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (13.7 mg, 0.0211 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 11.5 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (12.5 mg, 89.7%) as pale yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 9.76 (s, 1H), 8.67 (br s, 2H), 8.62 (s, 1H), 8.10 (dd, J=4.6, 1.4 Hz, 1H), 7.94 (dd, J=7.6, 1.6 Hz, 1H), 7.53 (d, J=8.7 Hz, 2H), 7.49-7.47 (m, 1H), 7.41-7.29 (m, 4H), 7.25 (t, J=7.8 Hz, 1H), 7.19-7.08 (m, 3H), 6.88 (dd, J=7.8, 1.4 Hz, 1H), 6.73 (dd, J=8.0, 4.6 Hz, 1H), 2.90 (s, 3H), 2.61-2.48 (m, 4H), 2.25-2.12 (m, 1H), 1.89-1.76 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationThe precipitated solids were collected by filtration
  3. washwashed with ether

Sources & evidence

ORD record
ord-e79ceee29d1842be9631cf7e17e2b49b
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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